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Stewart

$282+ Cheap flights from Trinidad to New Windsor (SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
POS — SWF
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Trinidad to Stewart

Keep the following information in mind while searching for Trinidad to Stewart flight deals. Data was last updated January 15, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Popular in

August

Cheapest in

February

Average price

$435
Provider with most accurate pricing for Port of Spain Piarco Intl-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-New York (NYC) flights.
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find flight deals from Trinidad to Stewart

One-way flights from Trinidad to Stewart
Search for one-way flight options from Trinidad to Stewart. Find affordable one-way fares based on user searches. Data last updated January 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2910:10 am
POS
-
SWF
1 stop25h 09m
Multiple Airlines
Deal found 1/14$282
This Kiwi.com deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/279:10 am
POS
-
SWF
3 stops51h 23m
Multiple Airlines
Deal found 1/15$369
This Kiwi.com deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/109:10 am
POS
-
SWF
3 stops48h 09m
Multiple Airlines
Deal found 1/12$378
This Kiwi.com deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/219:10 am
POS
-
SWF
3 stops50h 09m
Multiple Airlines
Deal found 1/15$383
This Kiwi.com deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/249:10 am
POS
-
SWF
3 stops50h 09m
Multiple Airlines
Deal found 1/15$397
This Kiwi.com deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:13 am
POS
-
SWF
3 stops33h 18m
Multiple Airlines
Deal found 1/12$402
This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2210:10 am
POS
-
SWF
2 stops25h 21m
Multiple Airlines
Deal found 1/14$410
This Kiwi.com deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/272:28 pm
POS
-
SWF
3 stops45h 34m
Multiple Airlines
Deal found 1/12$414
This Kiwi.com deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/209:10 am
POS
-
SWF
3 stops51h 23m
Multiple Airlines
Deal found 1/15$431
This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:13 am
POS
-
SWF
2 stops32h 49m
Multiple Airlines
Deal found 1/14$451

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
Use the filters below to find and compare flights from Trinidad to New Windsor that are best for you.

Fly from

Trinidad

Fly to

Stewart

Route

Depart

Return

Price

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Thu 1/29

10:10 am-10:19 am

1 stop25h 09m

$282

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Tue 1/27

9:10 am-11:33 am

3 stops51h 23m

$369

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Tue 3/10

9:10 am-9:19 am

3 stops48h 09m

$378

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Wed 1/21

9:10 am-10:19 am

3 stops50h 09m

$383

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sat 1/24

9:10 am-10:19 am

3 stops50h 09m

$397

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Wed 2/25

3:13 am-11:31 am

3 stops33h 18m

$402

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Sun 3/22

10:10 am-11:31 am

2 stops25h 21m

$410

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 2/27

2:28 pm-11:02 am

3 stops45h 34m

$414

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 2/27

3:13 am-11:02 am

2 stops32h 49m

$451

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Best time to book a flight from Trinidad to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Trinidad with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Trinidad to New Windsor

What is the cheapest month to book a flight from Trinidad to New Windsor?

Currently, January is the cheapest month in which you can book a flight from Trinidad to New Windsor (average of $164). Flying from Trinidad to New Windsor in October is currently the most expensive (average of $286). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Trinidad to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Trinidad?

    For a flight from Trinidad to New Windsor, you will be flying into Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

  • Can I find deals for flights from Trinidad to Stewart that include hotel bookings?

    Yes. In addition to deals on Trinidad to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Trinidad to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Trinidad to Stewart.

  • Can I find deals for business class flights from Trinidad to Stewart?

    Yes. Cheapflights offers flight deals from Trinidad to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Trinidad to New Windsor?

    Currently, January is the cheapest month in which you can book a flight from Trinidad to New Windsor (average of $164). Flying from Trinidad to New Windsor in October is currently the most expensive (average of $286). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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